(4aR,6aS,6bR,8aS,12aS,12bR,14bS)-8a-(1H-imidazole-1-carbonyl)-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-2-carbonitrile

• ChemBase ID: 163865
• Molecular Formular: C34H43N3O3
• Molecular Mass: 541.72352
• Monoisotopic Mass: 541.33044225
• SMILES: C1(=C[C@]2([C@H](C(C1=O)(C)C)CC[C@@]1(C2=CC(=O)[C@H]2[C@]1(CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)n1cncc1)C)C)C)C#N
• Canonical SMILES: N#CC1=C[C@@]2(C)[C@H](C(C1=O)(C)C)CC[C@@]1(C2=CC(=O)[C@H]2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)n1cncc1)C
• InChI: InChI=1S/C34H43N3O3/c1-29(2)10-12-34(28(40)37-15-14-36-20-37)13-11-33(7)26(22(34)18-29)23(38)16-25-31(5)17-21(19-35)27(39)30(3,4)24(31)8-9-32(25,33)6/h14-17,20,22,24,26H,8-13,18H2,1-7H3/t22-,24-,26-,31-,32+,33+,34-/m0/s1
• InChIKey: ITFBYYCNYVFPKD-FMIDTUQUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6aS,6bR,8aS,12aS,12bR,14bS)-8a-(1H-imidazole-1-carbonyl)-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-2-carbonitrile
• IUPAC Traditional name: (4aR,6aS,6bR,8aS,12aS,12bR,14bS)-8a-(imidazole-1-carbonyl)-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-4a,5,6,7,8,9,10,12,12a,12b-decahydropicene-2-carbonitrile
• Synonyms: 1-(2-Cyano-3,12,28-trioxooleana-1,9(11)-dien-28-yl)-1H-imidazole; 2-Cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid imidazolide; CDDO-Im; RTA 403; TP 235; CDDO Imidazolide

Database IDs

• CAS Number: 443104-02-7
• PubChem SID: 162258000
• PubChem CID: 9958995

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 5.8017178
• LogD (pH = 7.4): 5.8024592
• Log P: 5.8024683
• Molar Refractivity: 155.2325 cm^3
• Polarizability: 60.142384 Å^3
• Polar Surface Area: 92.82 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 180-192°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C228090

CDDO Imidozolide (CDDO-Im) is a synthetic triterpenoid CDDO-Im inhibits fatty acid synthase expression and has antiproliferative and proapoptotic effects in human liposarcoma cells. Studies show that CDDO-Im is highly active in suppressing cellular prolif

REFERENCES

• Hughes, D.T. et al.: Cancer Invest., 26, 118 (2008)
• Place, A.E. et al.: Clin. Cancer Res., 9, 2798 (2008)
• Samudio, I. et al.: J. Biol. Chem., 280, 36273 (2008)